I'm a regular player on these social casinos and was disappointed to learn these aren't deductible! But it makes sense - I'm basically just buying entertainment. One thing to consider though - if you're a content creator or streamer who plays these games as part of your business, you might be able to deduct them as a business expense. That's what my accountant told me since I have a small YouTube channel where I review social casino games.

This is a great question that comes up a lot! The consensus here is correct - social casino purchases where you can't cash out real money are treated as entertainment expenses, not gambling losses. I've seen people get confused about this because it *feels* like gambling, but the IRS looks at whether there's actual monetary risk/reward. One thing I'd add is to be extra careful about record-keeping if you do have any legitimate gambling activities. The IRS can be pretty strict about documentation for gambling loss deductions, so you want to make sure you're not mixing entertainment expenses with actual gambling losses on your return. Keep those social casino receipts separate from any real gambling records to avoid any confusion during an audit. Also worth noting - if you're spending $2500+ on these games, you might want to consider whether that money could be better invested in tax-advantaged accounts like an IRA or 401k where you'd get actual tax benefits!

Called IRS yesterday - they said standard time is 4 weeks but could take up to 6 if theres any postal delays in your area

I'm in week 4 waiting for my paper check too. Called my local post office and they said there's been unusual delays with government mail in my area due to processing backlogs. Might be worth calling yours to see if there are any local issues. Really wish I had done direct deposit - lesson learned for next year!

Based on what everyone's sharing here, it sounds like you definitely need to get clarity on the actual 409A valuation from your company. The fact that HR is being evasive when you ask about the higher valuation number is a red flag - they should be transparent about this since it directly affects your tax liability. I'd recommend requesting the most recent 409A valuation report directly. As an employee with stock options, you have a legitimate need for this information to make informed decisions about exercising. If they won't provide it, that's concerning and might indicate the FMV is actually higher than your strike price. The timing question is crucial too. If your company is pre-IPO and growing quickly, waiting could mean a much larger AMT hit later. I've seen people get stuck with massive tax bills because they waited too long to exercise. The 83(b) election mentioned earlier is also critical if you're doing early exercise on unvested shares - missing that 30-day window can cost you thousands in additional taxes. One more thing to consider: even if the current 409A valuation equals your strike price, companies typically update these valuations every 12 months or after major funding events. So that spread could open up quickly.

You're absolutely right to push for transparency on this. As someone who's been through multiple equity compensation scenarios, I can tell you that companies are legally required to provide the FMV information used for tax purposes - it's not optional. Here's what I'd recommend: Send a formal email to both HR and your finance team requesting the specific per-share fair market value from your most recent 409A valuation, along with the date of that valuation. Reference that you need this information to properly calculate your AMT liability for tax planning purposes. If they continue to stonewall, escalate to your manager or even the CFO - this is a legitimate business need. Regarding timing, most companies do 409A valuations annually or within 12 months of a material event (like a funding round). If your company just raised money, they likely have a fresh valuation that reflects the new funding environment. The fact that there's a "higher number floating around" suggests the 409A was probably updated recently and may indeed be higher than your strike price. Don't let them keep you in the dark on something that directly affects your personal tax liability. You have every right to this information, and any reputable company should provide it without hesitation.

Another tip from someone who's been doing solo 401k for 7 years - keep really good records of your contributions year over year. The IRS has been increasingly auditing retirement accounts and with a solo 401k YOU are the plan administrator. I track mine in a spreadsheet with dates, amounts, and whether it's employee or employer contribution. Believe me, trying to figure this out retrospectively is a nightmare.

Great advice from everyone here! As someone who just went through my first year of solo 401k reporting, I can confirm that the lack of forms from custodians was definitely confusing at first. One thing I'd add is to make sure you understand the deadline differences too. Unlike IRAs where you have until the tax filing deadline (plus extensions) to make contributions, solo 401k employee deferrals must be made by December 31st of the tax year. However, employer contributions can be made up until your tax filing deadline including extensions. This timing difference caught me off guard in my first year - I thought I could make all my contributions by April 15th like with an IRA, but realized I had missed the window for additional employee deferrals. Luckily I could still max out the employer portion, but it's something to plan for going forward. Also seconding the advice about keeping detailed records. I use a simple spreadsheet tracking contribution dates, amounts, and type (employee vs employer). When tax time comes around, having everything organized makes the reporting so much smoother.

Based on the details you've provided, this looks like a classic case where the lump sum payment would be treated as taxable alimony income under the pre-2019 rules. Since the original divorce was finalized in 2014 and the payment is explicitly described as settling "spousal support obligations," the IRS would likely view this as a substitute for the monthly alimony payments your mother-in-law was receiving. The challenging part is that she'll need to report the entire $195,000 as income in the year she received it, which could push her into a higher tax bracket. A few strategies to consider: maximize any retirement contributions for 2025 to reduce her adjusted gross income, look into whether she qualifies for any tax credits based on her situation, and consider making estimated tax payments if she hasn't already to avoid underpayment penalties. One thing worth double-checking is whether the October 2024 settlement agreement contains any specific language about tax treatment. While it's unlikely to change the outcome given the circumstances, sometimes the exact wording can make a difference. You might also want to consult with a tax professional given the size of this payment and its potential impact on her overall tax situation.

I dealt with a very similar situation when my aunt received a lump sum buyout of her alimony payments last year. Her divorce was from 2012, so it fell under the old tax rules just like your mother-in-law's situation. One thing that really helped us was getting a written opinion from a tax attorney before filing. Even though the general consensus here is correct (that it's likely taxable as alimony), the attorney was able to review the exact language in both the original divorce decree and the buyout agreement to confirm there weren't any loopholes or alternative characterizations we could use. The attorney also helped us structure some tax planning strategies for the following year to help offset the big tax hit. We ended up doing things like timing the sale of some investments with losses to offset gains, and making sure she maximized any charitable deductions in the same tax year. The whole consultation cost about $500 but potentially saved thousands in taxes through proper planning. With a $195,000 payment, I'd definitely recommend getting professional help - the potential tax liability is just too large to risk making a mistake on the classification or missing out on legitimate tax reduction strategies.